Methanol → rac-(1S,2S,4R,5R,6R,7S)-7-(Methoxycarbonyl)tricyclo[3.2.2.02,4]non-8-ene-6-carboxylic acid

HRID 548353Notes

Reaction equation

HRID 548353 reaction equation
[CH:1]12[CH:12]=[CH:11][CH:7]([CH:8]3[CH:10]1[CH2:9]3)[CH:6]1[CH:2]2[C:3](=[O:14])[O:4][C:5]1=[O:13].[CH3:15][OH:16]>>[CH3:15][O:16][C:3]([CH:2]1[CH:1]2[CH:12]=[CH:11][CH:7]([CH:8]3[CH:10]2[CH2:9]3)[CH:6]1[C:5]([OH:4])=[O:13])=[O:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 2600324,4A,5,5a,6,6a-hexahydro-1H-4,6-ethenocyclopropa[f]isobenzofuran-1,3(3aH)-dione

Product 1

HCID 58339439rac-(1S,2S,4R,5R,6R,7S)-7-(Methoxycarbonyl)tricyclo[3.2.2.02,4]non-8-ene-6-carboxylic acidYield 94%

Conditions

Temperature
25 °C

Procedure

rac-(1R,2S,6R,7S,8S,10R)-4-Oxatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione (prepared as described in Example 51a, 0.86 g, 4.50 mmol) was dissolved in methanol (20 mL). The reaction was stirred at 25° C. for 72 h. The mixture was concentrated to afford a clear oil. Purification by flash column chromatography (Teledyne Isco RediSep column; 0 to 60% ethyl acetate in hexanes) afforded the desired product, rac-(1S,2S,4R,5R,6S,7R)-7-(Methoxycarbonyl)tricyclo [3.2.2.02,4]non-8-ene-6-carboxylic acid (0.94 g, 4.23 mmol, 94%) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 0.06-0.17 (2H, m), 1.26-1.38 (2H, m), 2.74-2.85 (2H, m), 3.15-3.19 (2H, m), 3.67 (3H, s), 5.85-5.86 (2H, m). LC-MS (ESI) calcd for C12H14O4 222.24, found 223.5 [M+H+].

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford a clear oil
  3. customPurification by flash column chromatography (Teledyne Isco RediSep column; 0 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c75dc3cb2da9473c9e96e0f4fa3465d1
Source dataset
uspto-grants-2011_05
Patent number
US07939524B2

Reaction notes

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